Water and hydrogen atom elimination from ionised n-propanol: Extraordinarily large kinetic isotope effects

Chemical Communications

Volumn , Issue 20, 1999, Pages 2111-2112

  Bowen, Richard D ^a   Mandeville, Simon J ^a   Trikoupis, Moschoula A ^b   Terlouw, Johan K ^b  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; ISOTOPE; PROPANOL; WATER;

ARTICLE; CHEMICAL REACTION KINETICS; IONIZATION;

EID: 0033592632     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906881c     Document Type: Article

References (31)

1. R. G. Cooks, J. H. Beynon, R. M. Caprioli and G. R. Lester, Metastable Ions, Elsevier, Amsterdam, 1973.
2. For reviews, see: D. H. Williams, Acc. Chem. Res., 1977, 10, 280; R. D. Bowen, D. H. Williams and H. Schwarz, Angew. Chem., Int. Ed. Engl., 1979, 18, 451; R. D. Bowen and D. H. Williams, in Rearrangements in Ground and Excited States, ed. P. DeMayo, Academic Press, New York, 1980, vol. 1, ch. 2.
3. For reviews, see: D. H. Williams, Acc. Chem. Res., 1977, 10, 280; R. D. Bowen, D. H. Williams and H. Schwarz, Angew. Chem., Int. Ed. Engl., 1979, 18, 451; R. D. Bowen and D. H. Williams, in Rearrangements in Ground and Excited States, ed. P. DeMayo, Academic Press, New York, 1980, vol. 1, ch. 2.
4. For reviews, see: D. H. Williams, Acc. Chem. Res., 1977, 10, 280; R. D. Bowen, D. H. Williams and H. Schwarz, Angew. Chem., Int. Ed. Engl., 1979, 18, 451; R. D. Bowen and D. H. Williams, in Rearrangements in Ground and Excited States, ed. P. DeMayo, Academic Press, New York, 1980, vol. 1, ch. 2.
5. The expression 'critical energy' corresponds conceptually to the term 'activation energy', A. Maccoll, Org. Mass Spectrom., 1980, 15, 225.
6. For examples of extremely large isotope effects in very small hydrocarbon ions, see: C. Lifshitz and L. Sternberg, Int. J. Mass Spectrom. Ion Phys., 1969, 2, 303; U. Lohle and Ch. Ottinger, J. Chem. Phys., 1969, 51, 3097; M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1970, 52, 978; L. P. Hills, M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1971, 54, 3834.
7. For examples of extremely large isotope effects in very small hydrocarbon ions, see: C. Lifshitz and L. Sternberg, Int. J. Mass Spectrom. Ion Phys., 1969, 2, 303; U. Lohle and Ch. Ottinger, J. Chem. Phys., 1969, 51, 3097; M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1970, 52, 978; L. P. Hills, M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1971, 54, 3834.
8. For examples of extremely large isotope effects in very small hydrocarbon ions, see: C. Lifshitz and L. Sternberg, Int. J. Mass Spectrom. Ion Phys., 1969, 2, 303; U. Lohle and Ch. Ottinger, J. Chem. Phys., 1969, 51, 3097; M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1970, 52, 978; L. P. Hills, M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1971, 54, 3834.
9. For examples of extremely large isotope effects in very small hydrocarbon ions, see: C. Lifshitz and L. Sternberg, Int. J. Mass Spectrom. Ion Phys., 1969, 2, 303; U. Lohle and Ch. Ottinger, J. Chem. Phys., 1969, 51, 3097; M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1970, 52, 978; L. P. Hills, M. L. Vestal and J. H. Futrell, J. Chem. Phys., 1971, 54, 3834.
10. For a review of the mechanistic significance of extreme isotope effects, see: A. Thibblin and P. Ahlberg, Chem. Soc. Rev., 1989, 18, 209.
11. F. W. McLafferty and F. Turecek, Interpretation of Mass Spectra, 4th edn., University Science Books, Mill Valley, California, 1993.
12. J. J. Zwinselmann, N. M. M. Nibbering, N. E. Middlemiss, J. H. Vajda and A. G. Harrison, Int. J. Mass Spectrom. Ion Phys., 1981, 38, 163.
13. T. Weiske and H. Schwarz, Chem. Ber., 1983, 116, 323; T. Weiske, H. Halim and H. Schwarz, Chem. Ber., 1985, 118, 495; T. Weiske and H. Schwarz, Tetrahedron, 1986, 42, 6245.
14. T. Weiske and H. Schwarz, Chem. Ber., 1983, 116, 323; T. Weiske, H. Halim and H. Schwarz, Chem. Ber., 1985, 118, 495; T. Weiske and H. Schwarz, Tetrahedron, 1986, 42, 6245.
15. T. Weiske and H. Schwarz, Chem. Ber., 1983, 116, 323; T. Weiske, H. Halim and H. Schwarz, Chem. Ber., 1985, 118, 495; T. Weiske and H. Schwarz, Tetrahedron, 1986, 42, 6245.
16. S. Hammerum and P. J. Derrick, J. Chem. Soc., Chem Commun., 1985, 996.
17. S. Ingemann, S. Hammerum and P. J. Derrick, J. Am. Chem. Soc., 1988, 110, 3869; S. Ingemann, S. Hammerum, P. J. Derrick, R, H. Fokkens and N. M. M. Nibbering, Org. Mass Spectrom., 1989, 24, 885; S. Ingemann, E. Kluft, N. M. M. Nibbering, C. E. Alison, P. J. Derrick, and S. Hammerum, Org. Mass Spectrom., 1991, 26, 875.
18. S. Ingemann, S. Hammerum and P. J. Derrick, J. Am. Chem. Soc., 1988, 110, 3869; S. Ingemann, S. Hammerum, P. J. Derrick, R, H. Fokkens and N. M. M. Nibbering, Org. Mass Spectrom., 1989, 24, 885; S. Ingemann, E. Kluft, N. M. M. Nibbering, C. E. Alison, P. J. Derrick, and S. Hammerum, Org. Mass Spectrom., 1991, 26, 875.
19. S. Ingemann, S. Hammerum and P. J. Derrick, J. Am. Chem. Soc., 1988, 110, 3869; S. Ingemann, S. Hammerum, P. J. Derrick, R, H. Fokkens and N. M. M. Nibbering, Org. Mass Spectrom., 1989, 24, 885; S. Ingemann, E. Kluft, N. M. M. Nibbering, C. E. Alison, P. J. Derrick, and S. Hammerum, Org. Mass Spectrom., 1991, 26, 875.
20. R. D. Bowen and A. D. Wright, J. Chem. Soc., Chem. Commun., 1991, 1055; 1992, 96; A. D. Wright and R. D. Bowen, Can. J. Chem., 1993, 71, 1073.
21. R. D. Bowen and A. D. Wright, J. Chem. Soc., Chem. Commun., 1991, 1055; 1992, 96; A. D. Wright and R. D. Bowen, Can. J. Chem., 1993, 71, 1073.
22. R. D. Bowen and A. D. Wright, J. Chem. Soc., Chem. Commun., 1991, 1055; 1992, 96; A. D. Wright and R. D. Bowen, Can. J. Chem., 1993, 71, 1073.
23. R. D. Bowen, A. W. Colburn and P. J. Derrick, J. Am. Chem. Soc., 1990, 113, 1132 and references therein.
24. B. F. Yates, W. J. Bouma and L. Radom, J. Am. Chem. Soc., 1984, 106, 5805.
25. For a review, see: S. Hammerum, Mass Spectrom. Rev., 1988, 7, 123.
26. F. Lossing, J. Am. Chem. Soc., 1977, 99, 7256.
27. R. D. Bowen and P. J. Derrick, J. Chem. Soc., Perkin Trans. 2, 1992, 1041.
28. J. W. Gauld and L. Radom, Chem. Phys. Lett., 1997, 275, 28.
29. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, An Initio Molecular Orbital Theory, Wiley, New York, 1986.
30. J. B. Foresman and A. Firsch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, PA, 1996, ch. 7.
31. H. F. van Garderen, P. J. A. Ruttink, P. C. Burgers, G. A. McGibbon and J. K. Terlouw, Int. J. Mass Spectrom. Ion Processes, 1992, 121, 159.